Benzylamine → Acetoacetobenzylamide

HRID 2847

Reaction equation

HRID 2847 reaction equation
CC1(C)O[C:6](=[O:8])[CH:5]=[C:4]([CH3:9])[O:3]1.[CH2:11]([NH2:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1(C)C=CC=CC=1>[CH2:11]([NH:18][C:6](=[O:8])[CH2:5][C:4](=[O:3])[CH3:9])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 793682,2,6-Trimethyl-4H-1,3-dioxin-4-one

Product 1

HCID 70159Acetoacetobenzylamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

9 ml (0.05 mol) of 2,2,6-trimethyl-4H-1,3-dioxin-4-one (diketene-acetone adduct) were added dropwise to a solution of 5.5 ml (0.05 mol) of benzylamine in 20 ml of toluene and the temperature was allowed to rise 70° C. The solution was refluxed for 2 h then the solvent was removed in vacuo. The crude product was triturated with ether obtaining 7.5 g of the title compound. M.p.=84°-86° C.

Workup

  1. customto rise 70° C
  2. temperatureThe solution was refluxed for 2 h
  3. customthe solvent was removed in vacuo
  4. customThe crude product was triturated with ether obtaining 7.5 g of the title compound

Sources & evidence

ORD record
ord-f260c158922847e2b6dce05f84aaf68d
Source dataset
uspto-grants-1998_03
Patent number
US05731322

Linked notes

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